I understand your point, but for some reason there's some corner of my brain that's interested in litigating this if you'll bear with me. I definitely think the color of nostalgia is a real thing, and for me that imprinting shows up the most in still having an inexplicable affinity for '90s nu metal that I can't really reconcile with any notion of sophisticated taste.
But I think sometimes you see the opposite thing too, where a rewatch or re-listen is very disappointing, and undermines your impression that something is great. So it's clear that at least some of the time the nostalgia effect falls away. And I like to think staying power after repeated watchings can testify to "classic" status. But I think the reason I'm interested in drawing distinctions here is because I don't like the idea that Deus Ex, the greatest game of all time imo, can be pointed to to vindicate modern day conspiracy theorists, like they are the same thing.
In fact, the next time Warren Spector is interviewed I hope someone asks how he feels about his game being invoked in that way.
I think I made the wrong point when I wrote about nostalgia. I don't mean so much "you're remembering the work as better than it was", but more "you remember the zeitgeist that made the work great".
I watched Macgyuver (my favourite childhood show) recently, and it was terrible, twenty minutes of filler for one cool engineering scene, way worse than I remembered it. However, it's not the show that's changed, it's that I forgot what the 90s were like and how cool Macgyuver was in that zeitgeist.
Similarly, it's not that the Matrix isn't great, it's that, if you watched it in its era, you may remember how unlike anything else it was. You can't know how groundbreaking it was unless you remember that era, otherwise it's just one movie of many.
I can't speak to your later points as I don't know what Deus Ex is about or how it's used to vindicate conspiracy theorists, unfortunately.
in fact liked it even more, as the "humanity lost a war against AI in the early 21th century" felt very current.